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Dr. Westchesterson & The Headband

Modern Day Yacht Rock

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Dr. Westchesterson's love for Yacht Rock has a lot to do with the fact that he's spent over 25 years summering on Block Island. It also has to do with his love of the sun drenched sounds of 70's California soft rock. After releasing his album Better Days Ahead the Dr. assembled a band comprised of some of New England's most sought after musicians. Over the course of a two hour show Dr. Westchesterson and The Headband treat audiences to note-perfect takes on the Better Days Ahead album tracks in addition to a finely curated selection of Yacht Rock classics by artists such as; Steely Dan, The Eagles, The Doobie Brothers, Kenny Loggins and more. 


Dr. Westchesterson's Hip Hop Show

New Old School Hip Hop

Dr. Westchesterson burst onto the scene in 2012 with the release of his viral music videos "413" and "I'm from Western Mass". The tracks made Dr. W an instant cultural icon around his home turf of W. Mass. Since then he's performed throughout New England bringing his electrifying brand of New Old School Hip Hop to the masses. Featuring mostly original material along with a few choice covers, fans of The Beastie Boys, Dr. Dre, A Tribe Called Quest and Jay-Z will instantly recognize the influences. This adult-themed, one man show packs a one-two punch with equal parts humor and high energy beats.


Dr. Westchesterson's Piano Bar

Cocktail Lounge Classics

Before Dr. Westchesterson was a Hip Hop icon and Yacht Rock legend he was a simple Piano Bar lounge singer crooning the classics. For over two decades his residency as house piano guy at Captain Nick's on Block Island earned the Dr. a faithful following. Focusing on popular music from the 60s-70s the Dr.'s repertoire consists of hits from Billy Joel, Elton John, The Beatles, Bob Dylan, The Band, Tom Waits, Van Morrison and more! The Dr.'s piano style combines a precision derived from his classical roots with a loose New Orleans vibe a la Dr. John and Professor Longhair. Vocally, Dr. Westchesterson deftly switches gears between styles. One minute he's triumphantly belting out the high notes in Tiny Dancer the next he's gently crooning a James Taylor song to a pin-drop silent room. This three-hour long, one man show is perfect for the liveliest sing along bar setting or the sultriest cocktail lounge environment.

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